Playing Off of Your Insecurities
by MyLaWo
Summary: Quinn Fabray is a powerful businesswoman in Washington, D.C. She's also a womanizer who doesn't give a single fuck about other women's feelings beyond sex. That is until she meets Santana at a bar and she starts second guessing herself. (G!P Quinn)
1. Quinn Fabray

**AN: Okay first, am I tripping or is that bar/line break thing gone? I might be tripping but okay. Second, I clearly didn't updated when I said I would because of some personal issues but here it is! This first chapter is just some background on Quinn and the next chapter will be longer. Reminder that Quinntana is not the endgame as of now and Quinn is the main focus! Okay hope you enjoy and feel free to leave reviews!**

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Quinn Fabray has known since the young age of 7 that she could get anyone to do _almost_ anything she wanted and by the times she was 14 she had perfected the art of lying and manipulating to get _absolutely_ anything she desired. It wasn't a hard thing to master considering she learned by observing her father. Russell Fabray was one of the most powerful and influential men in DC because of the many businesses he owned and the people he knew. When Quinn turned 26 she inherited all of them becoming the sole heir of Fabray  & Co.

Growing up as an only child meant that Quinn was spoiled but her parents still made her work hard and earn the things she wanted because while she was able to manipulate and lie to everyone else, she respected her parents too much to do the same to them. Quinn knew she was going to inherit her father's company so she always focused on her grades in school and nothing else, meaning she didn't have time for friends. At least until her senior year where she met _her_ and experienced, what she believed to be, her first love but also ended up being her first, and last, heartbreak at the end of the year when _she_ learned about Quinn's extra appendage.

After ending her senior year on a bad note she decided to leave DC so she could focus on school. It was an easy choice for Quinn to go to Columbia, after getting accepted and offered a full academic scholarship, and plus she loved the thought of New York. Going to New York might have been the best, or worse depending on who you asked, decision Quinn has ever made. It's where she allowed herself to simply be free and after getting her heart broken it's where she vowed to _never_ let it happen again.

For the next 4 years Quinn slept with a lot of women, some were younger than her while others were old enough to be her mom. She still maintained her grades and graduated at the top of her class but unlike high school, where she allowed herself to get her heartbroken, she stopped caring about others feelings and became known as a womanizer. Being rich helped because it allowed her to get away with a lot and she used it to advantage when it came to women. After graduating, at the age of 22, she stayed in New York until she was 25 and had to go back to DC to focus on business.

When Quinn returned to DC she tried to focus but who was she kidding, she loved women too much and after having her fair share of them in New York, she went back to her old ways. With the weight of her being the CEO of the company she became even more careless when it came to women and their feelings and simply used them as if they were nothing but toys. To her they were nothing but her play things and she let them know. Of course some grew attached and she let them because she knew that she could get them to do anything she wanted.

That was how she carried on for the next 3 years until she met a beautiful Latina working at one of her favorite bars.


	2. First Time

**AN: Holy shit I think I owe you guys an explanation and even though I usually hate author notes I'm going to leave a short one for anyone who's curious. I've been dealing with some serious things that should be resolved by the end of the month BUT these things will have life changing effects when resolved. The only plus side will be the amount of time I'll have so that means regular updates for y'all. ALSO I know nothing about owing a business or anything like that so just try not to get mad at how I handle things. Now I'll stop there and leave you guys with this decently lengthy chapter.**

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The beginning of fall meant two things for Quinn: an increase in sales and a lot of trips to New York. All summer she has had to stay in DC in order to fix problems within the company caused by an incompetent employee she regrets hiring. The only time she' had to herself was during her birthday weekend in August, which she spent with her bestfriend Megan in LA, but the minute she was back and working so was the stress. With it now being September she was beyond tired and looking forward to her vacation in three weeks where she would hopefully be getting laid because a month was just too long for her to go without getting any and it showed in her mood. Right now most of her employees were waiting for the clock to strike 5, when she usually leaves, so that they could do their work without fear of being snapped at.

Quinn knew she has been in a horrible mood and the thought of staying until 5 wasn't helping so with it only being 4:30 she called her secretary, a younger girl named Marley who she has fucked a couple times, and let her know she'd be leaving.

Usually she would call Megan but she was currently in New York dealing with her own business so that left her with the options of going home to her empty million dollar penthouse or going to her favorite bar that was just two blocks away from her office. She started in the direction of her home before deciding that she earned a couple of drinks after the day she has had.

* * *

Walking into the bar/lounge Quinn headed to her favorite booth that was situated against the wall towards the left of the actual bar and on the opposite side of the kitchen. Her spot gave her the optimum view of the entire establishment while being hidden from most of the other costumers. She had been sitting for 3 minutes before she saw one of the most beautiful women she has ever seen come up to her table in a crisp waitress uniform.

"Hi, my name is Santana and I'll be helping you today. What can I get for you?" was the first thing that came out of the woman's mouth and for a moment Quinn forgot how to talk but she was a Fabray so while internally she was trying to figure out how someone could look so good, her facial expression turned from calm to flirtatious within seconds.

"Hello Santana," she said with a purr "tell Louis that Quinn is here and I'll take my usual." Quinn looked at her with a smirk in place. She watched Santana walk away, paying close attention to her plump ass in her black slacks, until she disappeared into the double doors that led to the kitchen. Just from the short interaction she knew she wanted her and with that a sly grin formed on her face.

It wasn't long before Santana came back to her table with a glass of white wine and a plate of chicken alfredo. Quinn could see that there was something different about her by the way her steps seemed a little timid and how her hands shook when she set the plate on the table. Louis had obviously informed Santana of who she was and for that she was happy because she could skip the introductory step.

"Here you go Ms. Fabray. Is there anything else I could get you?" Santana asked with a nervous smile on her face.

"No that will be all, unless you're on the menu?" Quinn watched the way her cheeks turned a slightly rosy color while she turned her eyes towards the floor. Quinn didn't like the lack of eye contact so she cleared her throat and raised a perfectly arched eyebrow until she could see Santana's beautiful brown eyes again. "That was a serious question by the way but I'll give you until I'm done with my food for an answer."

Santana looked shocked at how straightforward she was being but this was nothing new to Quinn. She knew that sometimes she could be quite direct and most people saw it as impolite or something but she simply hated small talk and preferred to just be upfront. Some people loved her for being so forward while others hated it. She couldn't care either way.

Quinn stared at Santana until she received a quick "Ok" before the girl basically power walked back into the kitchen. She chuckled to herself before digging in to her food and enjoying the somewhat relaxing music coming from the speakers.

Twenty five minutes later her plate was empty and she was waiting for Santana, who she knows has only come out the kitchen twice to check on other customers, to come out with her check and an answer. Five minutes later and she saw her walk out with a somewhat neutral expression on her face.

"Here is your check Ms. Fabray." Santana said while looking just to the right of Quinn's eyes.

"Thank you." Quinn said while pulling out her wallet and placing her black American Express card in the checkbook. "Will you be off around 7:30?"

Again, she looked shocked but replied, "Uh yes I get off at 7 but I have plans."

Quinn laughed, "Well how about instead of whatever plans you have, you cancel them and go out with me instead?" She smirked as she saw Santana think about it thinking she would say yes but instead she ended up surprised.

"Sorry but I don't think I can do that." And with that she picked up the checkbook, walked towards the register behind the bar, swiped her card and returned all within 2 minutes.

Quinn watched, slightly put off, as she walked back and placed the checkbook on the table before walking away again. She placed her card in her wallet and pulled out a pen from her purse. Flipping over the check she wrote down a quick note, put a 100 dollar bill with the note, got up and left.

* * *

Santana walked over to the table and picked up the checkbook. She saw that check was sticking out so she opened it and the first thing she saw was the money and then the note under it.

-I hope I didn't scare you away with how forward I was being. I would just really like a night alone with you and my bed. If you end up bored with your plans and would like to have fun text me before 9. –xo Quinn

Santana couldn't help but let out a laugh of disbelief as she read the note over. Walking back to the bar she thought about what Louis told her and she honestly felt slightly stupid from being so clueless when the daughter of Russell Fabray had entered. Just about everyone in DC knew who the Fabrays were and the thought of Quinn wanting her made her think she was being punk'd. She thought Quinn was absolutely stunning and while she didn't know who she was when she first walked in she was amazed by her beauty. After talking to Louis and finding out that she was helping THE Quinn Fabray she couldn't help but feel nervous under her stare.

She had heard about Quinn's womanizing ways and while the offer was tempting she didn't think she could allow herself to simply be a one night stand. Not only were one night stands not her thing, she was kind of seeing someone named Amber and didn't want to let this mess it up. While they weren't exclusive she refused to stop talking to her even though she didn't feel too strongly for her. Santana knew she was beautiful and could get girls but she was still insecure when it came down to relationships. She had a tendency to go all out for someone only to get nothing in return but she rarely complained and had never broken up with any of her exes. It was always the other way around and she didn't know why so she tried to hold onto them as long as possible.

Santana looked at the note one more time before thinking 'fuck it' and putting the number in her phone and then crossing it off with a marker before places it along with the others under the register. Walking away she felt kind of guilty but considering her plans consisted of hanging with Amber's friends she thought maybe having the option of texting Quinn wouldn't be such a bad thing.

 **AN: Okay how was that? It's been so long since I've written anything but I hope this wasn't too bad. I'm still setting the stage for this story so this chapter and the next few will not be that long but the next update should be before next week. Now while I'll never change how my story is I am open to suggestions.!**

 **Now, what do y'all think Santana should do? Text or no text? Should she give in to Quinn so easily or no?**


	3. Frieday

**AN: HOLY SHIT! It's been so long and I hate super long author notes but I'm here to say that I believe I'll be able to update this regularly for real this time and by that I mean at least two updates every month, maybe more. Anyways my brain and thoughts aren't the same as they once were and because of that my original outline for this story is so different. It'll be less angsty than I first imagined. I'll be updating the summary ASAP! No beta and I didn't edit lol all mistakes are my own.**

 **Anyways, I hope you enjoy!**

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Quinn would be lying if she said she wasn't siting at home on a Friday night waiting for her phone to alert her of a new text. When she walked in her door she told herself that she would wait until 9 on the dot and it was now 8:45 and still nothing. She was laying on her cream futon in her study at home willing herself to be patient for the next 15 minutes but was finding herself restless.

For some reason she couldn't stop thinking about what a night with Santana could be like. The thought of having her spread eagle on her bed, her tan skin against her white sheets, and dripping wet had Quinn hard and straining against her pants. Her mind was constantly thinking of all the ways she would take Santana if given the chance and she had really hoped that she would have a text by now but glancing at the clock and seeing the clock strike 9 she couldn't help but let out a small sigh of disappointment.

A sigh and two blinks later, Quinn was up and moving to her climb the steps that lead to her loft on the second floor. She pushed open the two doors to her bedroom and was surrounded by white walls and a mix of white and black furniture. She walked over to her huge closet that was about half the size of her room and tried to decide if she should go out or call a woman over so she could dress accordingly, having already showered when she got home earlier.

15 minutes later and she walked out in some black boxer briefs, a black sports bra, black joggers and a white wife beater. She picked up her phone and scrolled through her contacts looking for one of her favorited and sent a text telling her to come over at 9:30. It wasn't a full minute later when she received a reply that simply read "okay" and all she could do is shake her head with a smile as she set about getting some wine out before walking into her main living room area. She dimmed the lights and turned on her 80 inch smart tv before sitting on her oversized grey couch and cutting on Netflix.

At 9:30 on the dot she heard a knock on her door and smiled, happy that at least someone could follow directions. Pausing the show she was mindlessly watching she walked over and opened her door. Hazel eyes meeting blue.

* * *

Santana was so fucking bored. She was sitting next to Amber on a lumpy green couch listening as Amber and her friends talked about bands and concerts and other things she didn't really care about as they sipped beers.

She looked at her phone and saw that it was 9:30; meaning they had been here for an hour already and she didn't know when they'd be leaving. Looking around at Amber's group of her friends she couldn't help but frown as she saw one girl in particular looking at Amber with what looked like longing and a small lustful smile. She looked at the girl she came here with only to her staring at her with a smile on her face.

She blinked then smiled, "What?"

"I was asking if you wanted to go to a concert with us next Saturday?" Amber asked with a grin.

"Sure babe," Santana said with a smile and tried to keep the blush off her face when she received a peck on the cheeky.

A smile and blush that left her face after a quick glance at the same girl that was looking at Amber earlier; only to be met with a frown and somewhat of a hurt look that made her brows furrow in confusion. She shook her head and decided to ignore it even though her gut told her not to.

* * *

"Jessica."

"Quinn."

And those were the only words spoken before Quinn grabbed a hand that was paler than her own before pulling the shorter woman in her door and towards the couch. She placed her directly in front of the huge couch before scooting until her back met the soft cushion of her couch. She raised a perfectly sculpted eyebrow in a silent command and watched as the brown haired woman strip down to white lace lingerie. She twirled a single finger and watched as Jessica slowly did a full 360, admiring her flat stomach and perky breast along with her full ass.

She felt herself grow semi hard and she couldn't stop the groan of appreciation escape her mouth when they finally came face to face again. Eyebrow arching once again, Quinn watched as Jessica dropped into a kneel with her legs apart, hands behind her back, and chin to her chest with eyes looking at the floor. Quinn smiled and couldn't help but let out a praise.

"Good girl," Quinn said but she wasn't done just yet. "Now let's see how long it takes for you to get me off with your pretty mouth and for every minute you take that's how many lashes you get plus 5. Is that understood?"

"Yes, Quinn." Jessica moaned the words out.

Quinn chuckled at the noise before standing up and taking off her joggers and wife beater. She looked down and the woman before her and couldn't help the twitch of her dick as she started to harden completely. She rubbed her right hand over her growing bulge and then groaned before placing her left hand in brown locks. She tightened her grip and grinned as her eyes locked on to blue, "You ready to start?"

* * *

Sometime around 10 more people came around and what started out as a boring hang out turned into a full blown college party in a matter of minutes.

It was now 11 and Santana was standing in the kitchen sipping her drink as she looked around for Amber. The last she saw her was 10 minutes ago when Santana left to use the bathroom only to come back to find the lumpy green couch occupied by a bunch of guys who looked to be pulling out weed, weed that she wouldn't mind smoking when she decided against it so she could look for Amber.

Another 10 minutes passed and Santana was starting to get yreally annoyed when she decided to say "fuck it" before going over to the guys and picking up a blunt. She threw a 10 on the table before grabbing a lighter and sparking up. It wasn't long before she felt relaxed and giddy.

It 12 when she saw Amber again. Santana was high as kite but the minute she saw her come down the stairs adjusting her belt followed by the same girl from earlier; the only thing she could do was laugh, thankful that she didn't drink any tequila or her reaction would be the opposite.

Santana stood up still laughing before walking up to Amber and delivering a slap to her left cheek before walking out. She'd be lying if she said she wasn't slightly hurt when she realized Amber didn't even try to deny anything or follow after her. So with another sigh she called a cab and then sat on the porch swing while waiting. She was happy to note that it didn't hurt as much this time because she didn't really like Amber that much.

As the cab approached for some reason she thought of Quinn and how she could've been getting to know her tonight. She got in the cab before scrolling through her contacts, she saw that it was now 12:15 in the morning and she remembered how the note said to text before 9. She went to lock her phone before her wonderful brain found the loophole and she pressed the call button instead. A smirk graced her face as she waited for Quinn to answer only for it to continue to ring and go to voicemail. The smirked slid off her face before she decided to try one more time.

The phone rang three times before she heard a click and a raspy, "Hello?"

* * *

 **Okay my last AN: On a scale of one to ten how graphic should I write Quinn's "encounters" with other women? 1 for as brief as possible and 10 for detailed as fuck!**

 **Here's how this story has changed: There will be no domestic abuse or violence, no dubcon, and the only "drug use" will be weed and alcohol. It will be more focused on the D/s relationship the two have. air will still have angst and Quinn will be a player for a while but Quinntana is 100% endgame!**


	4. Dazed

**AN:** I didn't mean to go so long without updating but I had this chapter prepared last month but somehow deleted it. I'm not 100% happy with this chapter but I wanted to give you guys an update. Next chapter will be atleast 3k words and I'm hoping to have it up before the 4th of July.

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Quinn took pride in her stamina and her size but Jessica was quite talented with her mouth. She was one of the few woman that she has played with that could take more than half of her in her mouth without gagging. She knew she was close but she refused to come before 10 minutes was up. She looked down when she felt hands on her thighs. It was a signal for her to take over, which she was happy to oblige. She placed her hands on the back of Jessica's leg before pushing the woman's head down slowly, making her swallow more of her cock.

It was right after the 10 minute mark when she came down Jessica's throat. Quinn had to take a moment to catch her breath before she stood up and looked at the woman panting while kneeling below her. She loved seeing a good looking woman kneeling with flushed cheeks, blown pupils, and wet lips. The twitching of her dick and a moan from Jessica reminds her of the promise she made. She pulls her boxer briefs up before looking down again.

"15 lashes. 10 with my hand and 5 with the brush. I want you to go down that hallway, enter the last room to your right, and lay down on your stomach with your legs together and hands by your side." Quinn commands before turning and walking into the kitchen, the sound of footsteps followed by the rustling of sheets letting her know that her rules are being followed. She walks over to the fridge and grabs two bottles of water before making her way to the same room her entertainment for the night was waiting for her.

The room Jessica was in can be considered her "Play Room" or "Dungeon" of sorts but it's a room that she uses barely once a month. The floors in her entire house were all hardwood but in here she had gray and white carpet and all of the bedding was white and the walls were painted a dark gray. The room also had it's own bathroom with was highly convenient for all parties involved.

Quinn entered the room and had to keep herself from mounting the girl from behind before she can turn her ass a nice healthy shade of red. Jessica was on her hands and knees, ass facing the door, and Quinn could already see how wet she is. She walks over to her left, where the wall is covered with tools to implement either pleasure or pain that are sitting on shelves, and grabs a wooden brush before walking over to bed and looking down at the pale woman before her. She kneeled next to her hips, setting the brush and waters on the table besides the bed.

"I want you to count out loud for me." Is the only warning before she brings down her right hand in a quick yet controlled hit. It isn't until she hears a breathy " _one!_ ," that she allows the next four hits to follow in a quick succession, alternating between cheeks, and the " _two!, three!, four!, five!_ -" that comes out in little moans lets her know that she's warmed up enough so she slows down to admire the pink shade of Jessica's ass. The next hit brings out a " _-siX!_ " that's followed by a squeak and then a moan that causes Quinn's hand to sting slightly but she loves it. She makes sure to steadily increase the force so that her tenth hit brings out a " _TEN! Ohmygod!_ " And a loud groan that Quinn would mistake for pain if not for the fact that Jessica is dripping all over her sheets. She brings down both hands to rub lightly and to calm them both down a little before the next part.

"5 left with brush but don't count out loud this time." She picks up the brush with her right hand while her left hand rubs Jessica's ass until she feels her body relax. Quinn looks down at Jessica again but instead she imagines darker skin, darker hair, and a smaller but still full little ass.

 _Santana's_ full little ass.

 **No.**

 _Focus._

She blinks, 1-2-3 times, and then brings the brush down to her right cheek followed by the left. The next two are directed at her sit spots which makes her groan and wriggle a little. Quinn pauses until she's able to lay still again even though her chest is heaving. The last hit is the hardest and the "Fuck!" that Jessica accidentally lets out before her body starts to shake from the force of her orgasm has Quinn grinning with pride. She drops the brush before reaching the lotion to help with the sting Jessica will feel tomorrow.

"I'm going to rub some of this on your ass and then I'm thinking a shower for you before we call it a night, yeah?" Quinn asks and all she gets is a nod in return. Usually she would be fucking her like there's no tomorrow but she isn't one to fuck someone while thinking of someone else, at least not anymore. Been there, done that. Instead she straddles the back of Jessica's thighs and takes her time rubbing in the lotion, enjoying the little noises she makes.

* * *

It's the sound of her phone vibrating on her bedside table the has her jolting into a sitting position at 12:16 am but before she can reach for it, it stops, for all of three seconds, and then it's vibrating again. She answers. "Hello?"

A shaky breath is the first sign that a person is actually there on the other line and then there's the sound of a horn followed by a loud scratching noise in her ear that causes her to pull the phone away but she can distinctly hear the loud curse of a "FUCK!" that has her clicking her tongue in annoyance. She's three seconds away from hanging up when "Hi… this is Santana" is rasped into her hear and just like that she's wide awake.

"I'm pretty sure it's past 9 o'clock." While she's happy to hear from Santana, she is still slightly annoyed by being blown off.

Santana is taken aback by the clear annoyance she hears in Quinn voice. She's currently sitting in a stinky cab, wondering why she didn't get an Uber instead, and her phone is cracked from dropping it after hearing Quinn's voice. This night was not turning out how she hoped it would but she was still a little too high to care. "I'm pretty sure you said I had to text before 9 and I'm calling. Should I hang up?"

"NO!" Quinn blurted out without even thinking. She needed to get off the phone before her mouth decided to take over again. " I mean, how about tomorrow we give this another try? I'm free after 2 pm, how about you?"

Santana was not expecting for Quinn to want to see her again after she ignored her request or more like demand, earlier, she stared at her phone in disbelief for a few seconds before her curiosity won out, "I'll be free." She decides not to question Quinn at the moment.

"Okay, I'll text you the details tomorrow, see you then. Goodnight Santana." Quinn hangs up before tossing her phone on the other side of her bed, looking at it with a dopey smile on her face. Hopefully she'll be getting laid tomorrow night.

* * *

Santana's cab pulls up to her apartment just as Quinn hangs up. She pays the fare before getting out and entering the building. She silently thanks herself for not drinking as she starts climbing the three flights of stairs that leads to her door.

After unlocking, and then double checking to make sure it's locked after she enters, she's met with darkness. The usual.

She uses her memory to walk to the kitchen before she cuts on the light in there. She has a serious case of cotton mouth going on that some ginger ale would fix right up. Pouring herself a glass and grabbing a small bottle of water, she walks to her room. Clothes and shoes were scattered on the floor but she couldn't be bothered with that at the moment. All she wanted to do was sleep and not think.

Although her mind seems to have other plans. She couldn't help but think of Quinn as she took off her jeans and climbed into bed. The woman was a mystery to her. Not once did she think she would find herself in this situation. The only thing she remembers hearing about Quinn was that she slept with a lot of women and had money. She wasn't sure what someone like Quinn would want with her.

Santana isn't sure what she signed up for tomorrow but she's hoping she won't be regretting it this time tomorrow.

* * *

 **AN:** Next chapter will be pure Quinntana. It probably seems like there's a lot of details missing but I swear everything you're probably wondering will most likely be answered soon! Now, feel free to leave reviews and ideas!

p.s. I'm thinking of starting a AU Pezberry story when I reach the 10 chapter mark with this one. Would anyone be interested in that?


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